Calico Jack Rackham was an English pirate operating in the Caribbean area during the early 18th Century. His name derives from his practice of wearing colorful patchwork shirts made of printed calico fabric. Calico Jack is best remembered for his association with the Caribbean’s two most famous female pirates, Anne Bonny and Mary Read.

Calico Jack originally served as a quartermaster under another pirate, Charles Vane. When Vane decided to run from a battle with a much larger ship rather than fight, his crew became enraged. The crew members voted to relieve Vane from captaining and promote Jack Rackham in his place. It is debatable whether this constitutes a mutiny or not, as many ships operated under a democratic system in which a simple vote, rather than conspiracy or a coup, could remove the captain from office. Vane was given a small ship and departed peacefully.

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In 1719, Jack Rackham decided to accept a pirate amnesty offered by Woodes Rogers, the governor of New Providence in the Bahamas. Calico Jack may have intended to retire from the pirate life, but instead began a torrid affair with Anne Bonny, the wife of a local sailor. When the romance was discovered and brought to the Governor by Anne’s husband, Jack Rackham offered a divorce-by-purchase, which would have effectively ended the marriage and saved Anne from legal punishment. Anne, horrified that she could be bought and sold, and refusing to return to her husband, escaped aboard Calico’s ship and probably convinced him to resume his piracy.

Calico Jack and Anne Bonny began preying on small merchant ships for plunder with some success. Accounts vary, but either as a prisoner or already working on the ship in male disguise was another woman named Mary Read. Stories of the relationship between Anne, Mary, and Jack are many, and none considered definitively historical. Some suggest that Jack made the discovery of Mary’s gender when, jealous, he confronted her over how much time she spent with Anne. Others suggest that Mary and Jack were sometimes lovers, and her pregnancy upon capture was as a result of their relationship.

Whatever the truth of the relationship between the three pirates was, most accounts suggest they ruled the ship more or less equally. When the ship was finally taken by a notorious pirate hunter, Anne and Mary fought to the point of near exhaustion, while Calico and his men quietly surrendered. This led to a clear rift between them, which was never repaired. Calico was convicted of piracy and sentenced to death, but was allowed to briefly see Anne before his execution. Unsympathetic, Anne told him that if he had fought like a man, he wouldn’t be hung like a dog. On 19 November 1720, Calico and much of his crew were hanged in a cay and their bodies left as examples to other pirates.

In the recent blockbuster trilogy Pirates of the Caribbean several elements suggest that Captain Jack Sparrow was based partly on legends of Jack Rackham. Each historical pirate captain had their own version of the Jolly Roger flag, yet the one chosen for Sparrow’s ship is identical to Calico Jack’s. In the first film, Jack Sparrow is portrayed as a small time, unsuccessful pirate, whose captaincy is constantly question. Calico Jack never rose above mediocre success, and his rise to captaincy is tainted by accusation of mutiny. While this theory has never been confirmed by filmmakers, it is possible that Calico Jack has risen again, at least as an inspiration to a great cinematic character.

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